We thank the CNRS and the Université Paris-Sud (Fellowship to R.B.) for financial support, and Didier Gori for HPLC analysis.
FeCl3-Mediated Friedel–Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines†
Article first published online: 4 NOV 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 50, pages 12546–12550, December 7, 2012
How to Cite
Beaud, R., Guillot, R., Kouklovsky, C. and Vincent, G. (2012), FeCl3-Mediated Friedel–Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines . Angew. Chem. Int. Ed., 51: 12546–12550. doi: 10.1002/anie.201206611
- Issue published online: 4 DEC 2012
- Article first published online: 4 NOV 2012
- Manuscript Received: 16 AUG 2012
- Université Paris-Sud
- diazonamide A;
IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl3 features a rare example of the electrophilic reactivity of the indole core in a Friedel–Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent.